Why are ketones/aldehydes more oxidized than alcohols?

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Discussion Overview

The discussion centers around the oxidation states of ketones and aldehydes compared to alcohols, exploring the reasons behind the classification of these compounds in terms of oxidation. The scope includes theoretical reasoning and chemical principles related to oxidation and reduction processes.

Discussion Character

  • Technical explanation
  • Conceptual clarification
  • Debate/contested

Main Points Raised

  • Some participants suggest that the presence of double bonds in ketones and aldehydes allows oxygen to exert a stronger pull on electrons, contributing to their higher oxidation state compared to alcohols.
  • One participant proposes assigning oxidation numbers to carbon in methanol and methanal as a method to understand the oxidation process.
  • Another participant states that the removal of hydrogen during the conversion from alcohol to aldehyde represents an oxidation process.
  • It is mentioned that the more oxygen bonds a carbon has, the more oxidized it is, with carbon dioxide being the most oxidized form in this context.
  • Some participants express uncertainty about oxidation states and seek clarification on how to evaluate them, indicating a need for more accessible explanations than those found online.

Areas of Agreement / Disagreement

Participants express varying levels of understanding regarding oxidation states, with some agreeing on the general principle that more oxygen bonds indicate higher oxidation. However, there is no consensus on the best method to evaluate oxidation states or the specifics of the oxidation process.

Contextual Notes

Some participants mention limitations in their understanding of oxidation states, indicating a reliance on high school knowledge and a desire for clearer explanations. There are references to online resources that may not fully address participants' questions.

Who May Find This Useful

This discussion may be useful for students or individuals interested in organic chemistry, particularly those seeking to understand oxidation states and redox reactions involving alcohols, ketones, and aldehydes.

hivesaeed4
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I thought that the reason was the presence of a double bond would allow oxygen to exert a stronger pull on the electrons making the co bond as compared to when their was only a double bind between the two but then I remembered that inductance happens only through sigma bonds So why are ketones/aldehydes more oxidized as compared to alcohols?
 
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Many ways of skinning that cat.

First, and the simplest one - try to assign oxidation numbers to the carbon in methanol and methanal.

Can you write reaction equation of the R-CH2OH (a general primary alcohol) being converted to R-CHO (a general primary aldehyde)? What is removed from the alcohol molecule? How is the removed substance related to oxidation/reduction processes?
 
Yep. Think in terms of oxidation state of the carbon atom.
 
Well you remove hydrogen and so that in itself is oxidation.

But I don't remember the oxidation states/numbers. I learned them in high school and don't exactly remember them. Why don't you tell me how to evaluate the oxidation state of the carbon atom. I tried understanding it from other online sources yet I didn't really understand it and am pretty sure that you guys would do a better job at it than websites do.
 
The more oxygen bonds a carbon has the more oxidized it is. An alcohol has one and ketones or aldehydes have two. Carbon dioxide has four and represents the most oxidized form of carbon in this series. A little different than memorizing the oxidation numbers of atoms you saw back in HS.
 
hivesaeed4 said:
But I don't remember the oxidation states/numbers.

I tried understanding it from other online sources yet I didn't really understand it and am pretty sure that you guys would do a better job at it than websites do.

Really? I already prepared a website that explains these things, why do you think I will be better here than there:

(...)
Oxygen in almost all compounds has oxidation number -2.
Hydrogen in almost all compounds has oxidation number +1.
(...)
Last rule says that the charge of the ion or molecule equals sum of oxidation numbers of all atoms.
 
Thanks. By the way what was the name of the website your talking about Borek? I'd like to visit it. (I really didn't know you created one).
 
Thanks. Nice website.
 

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